Methyl iodide → 2-(1-Methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine

HRID 1038125Notes

Reaction equation

HRID 1038125 reaction equation
[CH2:1]([Sn:5]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([OH:15])([CH3:14])[CH3:13])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH3:26]I>C1COCC1.CCOC(C)=O>[CH3:26][O:15][C:12]([C:8]1[CH:7]=[C:6]([Sn:5]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=[CH:10][N:9]=1)([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 866301822-(4-Tributylstannanyl-pyridin-2-yl)-propan-2-ol

Product 1

HCID 866301812-(1-Methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-tributylstannanyl-pyridin-2-yl)-propan-2-ol 12AO (0.12 g, 0.27 mmol) in THF (2 ml) was added in a dry NaH (0.02 g, 0.54 mmol). Reaction mixture was stirred for 20 min at r.t. It was cooled to 0° C. and CH3I (0.02 ml, 0.32 mmol) was added drop wise. After 30 mins at 0° C., reaction mixture was warmed up to r.t. It was diluted with EtOAc (15 ml) after 2 hr and washed with water (2×3 ml) and brine (5 ml). Organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified on silica gel eluting with 1/4 EtOAc/Hexane to give the desired product 2-(1-methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine 13AO (0.1 g, 88%).

Workup

  1. customReaction mixture
  2. temperatureIt was cooled to 0° C.
  3. waitAfter 30 mins at 0° C.
  4. customreaction mixture
  5. temperaturewas warmed up to r.t
  6. washwashed with water (2×3 ml) and brine (5 ml)
  7. dry with materialOrganic extracts were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified on silica gel eluting with 1/4 EtOAc/Hexane

Sources & evidence

ORD record
ord-5eba0317a573493bab3dde349a172398
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…